According to Bloomberg Business, 2025 was defined by Oracle co-founder Larry Ellison’s aggressive moves in AI and media. On January 21, a day after Trump’s inauguration, Ellison joined a White House announcement for a $500 billion AI infrastructure plan called Stargate. By summer, OpenAI inked a deal worth around $300 billion to rent computing from Oracle. In September, Ellison’s net worth jumped $89 billion in a single day to $388 billion, briefly making him the world’s richest person. He then backed his son David’s Skydance Media in its takeover of Paramount and a subsequent hostile bid for Warner Bros. Discovery, offering to personally guarantee $40.4 billion in financing for the potential deal after it was initially rejected.
Ellison’s All-In AI Bet
Here’s the thing: Larry Ellison famously missed the cloud boat. Now, he’s trying to own the AI harbor. Oracle is spending like crazy on data centers, so much that its cash flow went negative for the first time in decades. That’s a huge, risky bet. But the payoff? A $300 billion commitment from OpenAI. Basically, Ellison is building the world’s most expensive hotel and just signed OpenAI to the biggest room rental in history. The problem is, that makes Oracle incredibly dependent on one tenant. If AI spending slows or OpenAI stumbles, Oracle’s whole strategy looks shaky. Investors are clearly nervous, which is why the stock—and Ellison’s fortune—has been on a roller coaster.
The Hollywood Family Business
And then there’s the other, equally risky bet: his son’s career. Ellison has moved from dabbling in his kids’ movies to bankrolling a media empire. Financing the Paramount deal was one thing. But personally guaranteeing over $40 billion for a hostile run at Warner Bros.? That’s next-level. It’s the kind of move he pulled in business, like with PeopleSoft, but now it’s for family. It raises a big question: is this savvy investing, or is it just a billionaire dad writing a blank check? Warner Bros. doubted they could deliver the equity, so Ellison stepped in with his personal balance sheet. That’s a ton of pressure, even for a fortune measured in hundreds of billions.
The Wealth Trap
So Ellison is worth nearly $250 billion, but most of that is tied up in Oracle stock. That $40.4 billion guarantee is a promise to have liquid cash if called. Could he sell stock? Sure. But selling that much would crater Oracle’s share price, which is the foundation of his wealth. He could pledge more shares, but that adds more leverage to an already debt-fueled situation. It’s a classic billionaire bind—paper wealth versus actual spending power. His fortune swung wildly in 2025, proving it’s not Monopoly money, but it’s also not all sitting in a checking account. This guarantee shows he’s willing to put his entire legacy on the line, twice over: for AI and for family.
Defining a Volatile Era
Look, Elon Musk is always news. But in 2025, Ellison’s story captured the two biggest, most volatile games in town: the AI arms race and the media consolidation scramble. He’s 81 and playing with more fire than ever. He’s not just collecting trophies anymore; he’s building (and potentially risking) the entire trophy room. Whether this year defines him as a visionary or a cautionary tale depends entirely on if those AI data centers print money and if his son can actually run a media conglomerate. One thing’s for sure: after decades in the background, Larry Ellison decided 2025 was his year to go all-in. And I think we’ll be talking about the consequences for a long time.
